Water → 1-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

HRID 250408

反応式

HRID 250408 の反応式
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](O)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:22])=O.O>C(#N)C>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:22])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 3

HCID 962WaterHCID 24613Phosphorus oxybromideHCID 1784508431,4-Dihydroxy-isoquinoline-3-carboxylic acid butyl ester

生成物 1

HCID 860145411-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester収率 3.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

2 g (7.7 mmol) of 1,4-Dihydroxy-isoquinoline-3-carboxylic acid butyl ester (from Example D-20 b) dissolved in 100 ml of acetonitrile. 15.4 g (53.6 mmol) of phosphorous oxybromide added to solution and mixture stirred at 80° C. for 64 h. 100 ml of water was added to mixture, and mixture was removed from heat. Mixture was partitioned between ethyl acetate and water. Two phases were separated and the aqueous layer was extracted with ethyl acetate. Organic layers were combined, washed with brine, dried over magnesium sulfate, filtered, and evaporated. Residue was purified by silica gel flash chromatography to give 0.1 g (0.3 mmol) of product. 1H NMR (200 MHz, CDCl3) δ 11.89 (s, 1H), 8.41 (m, 1H), 8.25 (m, 1H), 7.84 (m, 2H), 4.49 (t, J=7.0 Hz, 2H), 1.87 (m, 2H), 1.47 (m, 2H), 1.00 (t, J=7.2 Hz, 3H).

後処理

  1. customwas removed
  2. temperaturefrom heat
  3. customMixture was partitioned between ethyl acetate and water
  4. customTwo phases were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customResidue was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-10cff72e97344bb4b8e20239bd6c170d
出典データセット
uspto-grants-2011_01
特許番号
US07863292B2

関連ノート

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